A preorganized macrocycle based on a bicyclic guanidinium subunit with six convergent hydrogen bonds for anion recognition

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 1033-1036

  Alcázar, Victoria ^a   Segura, Margot ^a   Prados, Pilar ^a   De Mendoza, Javier ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BICYCLO COMPOUND; CHLORIDE ION; GUANIDINE DERIVATIVE; PHOSPHATE;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032568127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10696-7     Document Type: Article

References (12)

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5. c) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511.
6. d) Andreu, C.; Galán, A.; Kobiro, K.; de Mendoza, J.; Park, T. K.; Rebek, J., Jr.; Salmerón, A.; Usman, N. ibid. 1994, 116, 5501.
7. 4. See for example Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072, and references therein.
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9. 6. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151.
10. 3).
11. 9 and subsequent heating afforded the corresponding bis-isocyanate. One-pot macrocyclization to 2d took place by addition of 5 (23% overall yield). The (R)-1,1'-binaphthyl-2.2'-phosphate complex 2e was obtained by single liquid-liquid extraction from a dichloromethane solution of 2b and an aqueous solution of sodium (R)-1,1'-binaphthyl-2,2'-phosphate.
12. 9. Hengge, A. C.; Cleland, W. W. J. Am. Chem. Soc. 1991, 113, 5835.